Ammonia → Butyramide, 4-nitro-

HRID 1784334Notes

Reaction equation

HRID 1784334 reaction equation
[N+:1]([CH2:4][CH2:5][CH2:6][C:7]([O:9]C)=O)([O-:3])=[O:2].[NH3:11]>CO>[N+:1]([CH2:4][CH2:5][CH2:6][C:7]([NH2:11])=[O:9])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 25604Methyl 4-nitrobutyrate

Product 1

HCID 27314Butyramide, 4-nitro-Yield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of methyl 4-nitrobutyrate (8.83 g, 60 mmol) in methanol (20 mL) at 0° C. was added a solution of ammonia in methanol (7N, 30 mL). The solution was then warmed to room temperature and stirred at for 72 h. The solvent was evaporated and the residue was re-crystallized from ethyl acetate to give the title product (6.2 g, 78%). 1H NMR (acetone-d6): 6.86 (bs, NH, 1H), 6.28 (bs, NH, 1H), 4.59 (t, J=6.9 Hz, 2H), 2.36-2.30 (m, 2H), 2.28-2.20 (m, 2H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was re-crystallized from ethyl acetate

Sources & evidence

ORD record
ord-fdaf0a98c11b4a719b9bfd0aefb8ab0c
Source dataset
uspto-grants-2009_03
Patent number
US07504382B2

Reaction notes

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